Boron tribromide → HCID 178523484, compound

HRID 1093620Notes

Reaction equation

HRID 1093620 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:39])[CH2:16][NH:17][C:18]([C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31]CC4C=CC=CC=4)[CH:26]=3)[NH:22][N:21]=2)=[O:19])[CH2:11][CH2:10]1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:39])[CH2:16][NH:17][C:18]([C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=3)[NH:22][N:21]=2)=[O:19])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178523485HCID 178523485, compound

Product 1

HCID 178523484HCID 178523484, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of 5-(3-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide (0.19 g, 0.00035 mole) in dichloromethane was cooled to −70° C. 1 mL of a 1.6M solution of BBr3 in dichloromethane was then added dropwise with vigorous stirring. The reaction mixture was slowly brought to ambient temperature and stirring was continued at the same temperature for 1 hour. The reaction mixture was then cooled to −70° C. and ice cold water was added dropwise with stirring and while the mixture was slowly brought to ambient temperature. The product was extracted with dichloromethane and the organic layers were dried over sodium sulfate. The organic layer was collected and concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate to afford 0.071 g (45%) of 5-(3-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 454.16 (M+1)+, 94.25%, 1H NMR (DMSO-d6): δ 13.6 (s, 1H), 9.6 (s, 1H), 8.1 (s, 1H), 7.0 (m, 5H), 6.84 (d, 1H), 6.76 (d, 1H), 6.6 (m, 1H), 4.8 (s, 1H), 4.3 (d, 1H), 4.1 (d, 2H), 3.8 (d, 1H), 3.7 (s, 1H), 3.2 (m, 1H), 2.8 (m, 1H), 1.95 (m, 2H), 1.3 (m, 2H).

Workup

  1. customwas slowly brought to ambient temperature
  2. additionice cold water was added dropwise
  3. stirringwith stirring and while the mixture
  4. customwas slowly brought to ambient temperature
  5. extractionThe product was extracted with dichloromethane
  6. dry with materialthe organic layers were dried over sodium sulfate
  7. customThe organic layer was collected
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3daee23fba794e34a782d8f69ccb4af4
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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